ILOPROST

Search structure
Trade Names:
Synonyms:
Status: Approved (2004)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: B01AC11
UNII: JED5K35YGL

Structure
InChI Key HIFJCPQKFCZDDL-ACWOEMLNSA-N
Smile CC#CCC(C)[C@H](O)/C=C/[C@@H]1[C@H]2C/C(=C/CCCC(=O)O)C[C@H]2C[C@H]1O
InChI
InChI=1S/C22H32O4/c1-3-4-7-15(2)20(23)11-10-18-19-13-16(8-5-6-9-22(25)26)12-17(19)14-21(18)24/h8,10-11,15,17-21,23-24H,5-7,9,12-14H2,1-2H3,(H,25,26)/b11-10+,16-8+/t15?,17-,18+,19-,20+,21+/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C22H32O4
Molecular Weight 360.49
AlogP 3.54
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 8.0
Polar Surface Area 77.76
Molecular species ACID
Aromatic Rings 0.0
Heavy Atoms 26.0

Pharmacology

Action Mechanism of Action Reference
AGONIST Prostanoid IP receptor agonist ISBN DailyMed
Primary Target
IP receptor
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Lipid-like ligand receptor (family A GPCR) Prostanoid receptor
1 8-27 - 3-7 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Hypertension, Pulmonary 4 D006976 ClinicalTrials
Raynaud Disease 3 D011928 ClinicalTrials
Respiratory Distress Syndrome 3 D012128 ClinicalTrials
Shock, Septic 3 D012772 ClinicalTrials
Renal Insufficiency, Chronic 2 D051436 ClinicalTrials
Heart Arrest 2 D006323 ClinicalTrials
Multiple Organ Failure 2 D009102 ClinicalTrials
Lung Neoplasms 2 D008175 ClinicalTrials
Pulmonary Disease, Chronic Obstructive 2 D029424 ClinicalTrials
Scleroderma, Systemic 2 D012595 ClinicalTrials
Lung Neoplasms 2 D008175 ClinicalTrials
Myocardial Infarction 1 D009203 ClinicalTrials
Humeral Fractures 1 D006810 ClinicalTrials
Asthma 0 D001249 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Respiratory, thoracic and mediastinal disorders Cough 39.0
Nervous system disorders Headache 30.0
General disorders and administration site conditions Flushing 27.0
Surgical and medical procedures Vasodilation procedure 27.0
Respiratory, thoracic and mediastinal disorders Cough
Nervous system disorders Headache
General disorders and administration site conditions Flushing
Surgical and medical procedures Vasodilation procedure
Infections and infestations Influenza 14.0
Respiratory, thoracic and mediastinal disorders Cough
Gastrointestinal disorders Nausea 13.0
Musculoskeletal and connective tissue disorders Trismus 12.0
Vascular disorders Hypotension 11.0
Nervous system disorders Headache
Infections and infestations Influenza
General disorders and administration site conditions Flushing
Musculoskeletal and connective tissue disorders Trismus
Surgical and medical procedures Vasodilation procedure
Cardiac disorders Dizziness 8.0
Nervous system disorders Insomnia 8.0
Nervous system disorders Loss of consciousness 8.0
Gastrointestinal disorders Nausea
Vascular disorders Shock 8.0
Cardiac disorders Syncope 8.0
Musculoskeletal and connective tissue disorders Back pain 7.0
Investigations Laboratory test abnormal 7.0
Cardiac disorders Palpitations 7.0
Gastrointestinal disorders Vomiting 7.0
Investigations Blood alkaline phosphatase increased 6.0
Investigations Gamma-glutamyltransferase increased 6.0
Vascular disorders Hypotension
Nervous system disorders Insomnia
Musculoskeletal and connective tissue disorders Muscle spasms 6.0
Investigations Blood alkaline phosphatase increased
Cardiac disorders Dizziness
Cardiac disorders Haemoptysis 5.0
Vascular disorders Hypotension
Nervous system disorders Loss of consciousness
Gastrointestinal disorders Nausea
Vascular disorders Shock
Cardiac disorders Syncope
Gastrointestinal disorders Vomiting
Musculoskeletal and connective tissue disorders Back pain
Gastrointestinal disorders Glossodynia
Gastrointestinal disorders Glossodynia 4.0
Infections and infestations Influenza
Investigations Laboratory test abnormal
Cardiac disorders Palpitations
Infections and infestations Pneumonia 4.0
Musculoskeletal and connective tissue disorders Back pain
Cardiac disorders Dizziness
Investigations Gamma-glutamyltransferase increased
Cardiac disorders Haemoptysis
Investigations Laboratory test abnormal
Nervous system disorders Loss of consciousness
Musculoskeletal and connective tissue disorders Muscle spasms
Cardiac disorders Palpitations
Infections and infestations Pneumonia
Vascular disorders Shock
Cardiac disorders Syncope
Musculoskeletal and connective tissue disorders Trismus
Cardiac disorders Haemoptysis
Nervous system disorders Insomnia
Gastrointestinal disorders Vomiting
Investigations Blood alkaline phosphatase increased
Infections and infestations Pneumonia

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Respiratory, thoracic and mediastinal disorders
16.23
General disorders and administration site conditions
13.98
Cardiac disorders
11.94
Vascular disorders
7.77
Nervous system disorders
6.98
Gastrointestinal disorders
6.67
Injury, poisoning and procedural complications
4.88
Infections and infestations
4.57
Investigations
4.21
Metabolism and nutrition disorders
4.1
Musculoskeletal and connective tissue disorders
3.99
Surgical and medical procedures
2.38
Renal and urinary disorders
2.3
Psychiatric disorders
2.27
Skin and subcutaneous tissue disorders
2.16

Cross References

Resources Reference
CAS NUMBER 78919-13-8
ChEBI 63916
ChEMBL CHEMBL494
DrugBank DB01088
DrugCentral 1422
FDA SRS JED5K35YGL
Guide to Pharmacology 1895
KEGG D02721
PubChem 5311181
SureChEMBL SCHEMBL6083382
ZINC ZINC13587680
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